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Updated: November 6th 2015

Danny Woodhead could be an interesting player to acquire at the trade deadline.

When you and your friends signed up to join a Reality Sports Online league, you basically walked into the corn like in Field of Dreams. You weren’t necessarily sure what your initial strategy would be, but like other owners on the platform, you needed something more challenging, more engaging, basically an NFL-General Manager experience to break from the monotony of the everyday redraft league.

That’s exactly what you’re entrenched in and winning your league against your friends who you consider to be of above-average intelligence would be sweet, very sweet. Now you are at the point where you’ve meticulously managed your roster, strategized over rookie draft picks, made a deal or two, had some injuries, doled out some long term contracts, used your franchise tag and are ready to get raise your fist in the air for your first RSO championship.

The final piece to that roster puzzle to win your league may or may not come at the trade deadline, which is upcoming for several leagues. For non-contenders, the trade deadline becomes a chance to salvage some value (particularly future rookie draft picks or developmental players) for expiring players who won’t be retained but may help a contender. For contenders, the trade deadline is the last chance of the season to add a piece to help you for your championship run and potentially in future years.

The art of trading in your RSO league is all contextual and situation dependent which makes it the most complex set of scenarios you can face down the stretch in your attempt to gain lifetime bragging rights on your buddies because flags fly forever and your championship forever becomes part of league lore.

With that, let’s discuss some scenarios that you may be facing at the deadline, with a quick primer first.

Every now and then, we get Tweets asking about trades and whether or not you should do them. Let me start with some obvious advice-context really matters. Of course I’d rather have Julio Jones than Allen Robinson all things being equal. But if Robinson is on a second-round rookie deal and Jones costs me $30 million a year, Robinson’s value and point production allows so much flexibility that he’s more valuable than Jones to me. So make sure you consider the following when making any trade deadline deal:

1) Are You a Contender or a Non-Contender?

This can be a tricky question depending on what kind of league you are in. For instance, the top four records make the playoffs in my league plus another two wild-cards based on total points scored. So there’s multiple ways into the playoffs and teams that are on the fringe of one or the other can still be chasing these up until the last week of the season. Which makes our league super-exciting, but also hard to gauge how a team sees itself.

To me, total points scored is a good barometer at this point for how your team really is performing. I know there are bye weeks and everything, but if I learned anything in business school, it is the bigger the sample size, the better and a sample size of 30 typically takes out the randomness. So if you go to your standings and to the breakdown section, you’ll see your record if you played every team in your league each week. If your record is strong (sample size is definitely bigger than 30), it means you are putting up ample total points to contend in your league. If it is below .500, your overall record may mean you are getting lucky and you should be a seller.

Every owner has to decide where they fit at the deadline, but false optimism usually leads to straddling and backfires. So if you are playing for next season, act like it and get some assets that will help you more than having a few more weeks of Jonathan Stewart.

2) You don’t always have to get the best player in the deal, but make sure you are walking away with the best valued player in the deal.

Your lineup is like a puzzle and you have to put together the best lineup possible to win. Through the auction, rookie draft, in-season free agency and trades you’ve made thus far, you have to fit the player and the cap space you are targeting into your lineup. The natural inclination as your league trade deadline approaches is to go hard after the obvious names, a bunch of studs that you think can put you over the top, even if their contracts may not be good.

Hold off on this approach, unless the capital required is reasonable. The truth is if you are contending, you probably have a lot of solid pieces already. You don’t need two more years of Adrian Peterson at $25-30 million a year, you need Eric Decker at $5-$8 million a year for the next two-three years (or even one year). Plus the trade capital required to get a player like Decker will be way less (Editor’s Note: Goody indeed just traded Kendall Wright and his 2016 2nd Round Pick for Decker).

In my main league, I’ve seen rookie draft picks (particularly first rounders) move back and forth all season as teams have gone in and out of determining whether they are contenders. Meanwhile, the top two contenders (me included) have kept their picks intact and watched these teams make these moves.

Examples of these trades include Ben Roethlisberger’s owner panicking when he went down and trading his first for a one-year, $15.0 million Drew Brees deal (which so far, along with a solid cast has kept that team near the top of the standings), and a team traded a first rounder and Coby Fleener for DeMarco Murray (who was franchised in 2015). In total there have been fifteen trades so far this regular season in my 12-team league, most of which involving 2016 first-round draft picks.

I can with fair certainty say that save for myself and another top team, that most of the serious playoff contenders (and by that I mean the ones who can do serious playoff damage), don’t have draft picks to trade at the deadline to upgrade their teams. As a result, for me, it may be best to stand pat and not make moves unless this other top team does. Assuredly, assuming team health, trading first rounders seems to be out of the question when I can stand pat and still have a very good shot of being a top two team without making a deal. Thus in my particular situation, even though my draft pick figures to be towards the end of the first round, I’ve determined that it isn’t likely worth it to me to trade my 2016 first rounder to try to get a player to help ensure I win the championship this year. That doesn’t mean I don’t have other players I couldn’t move to get another piece (more on that later).

Please note that I’m more clingy to my rookie draft picks in a league with four-year rookie deals than three-year deals, especially since most owners are already one year into those deals. So if you are in the last year of an Eddie Lacy rookie deal for instance, getting something of substance back could be a coup.

4) Remember that you aren’t necessarily looking to “win the trade”, but rather get the value that propels your team to greater heights either now or later, depending on what your goal is.

So many trades don’t happen in fantasy leagues, because one owner is trying to get over on another. We’re all smart owners on this platform, so appropriate value the best way you know how. At the deadline you have two types of teams-contenders and non-contenders. Contenders want help now for the short-term (and maybe a year beyond) and non-contenders want future assets in the form of draft-picks or development players. If a non-contender decides that trading Martellus Bennett for three years of Jay Ajayi floats their boat, then other owners shouldn’t judge. The same thing goes for if a team makes a move going for the playoffs and it blows up in their face. Last year, a leaguemate did exactly that in my league and I think they’ll be way more careful at the deadline this year.

5) Throwing the farm and multiple good players for one great player doesn’t make as much sense in a league like this as it does in a redraft league.

I’ve seen some Tweets lately asking my views on multi-player trades. The one that stuck out to me was someone asking me if they should trade Jordan Matthews, Mike Evans (both on original rookie deals) and Gio Bernard for DeAndre Hopkins (3 years, $48.0 million) and a 2016 2nd rounder? Of course, I drilled in on context, but while this trade may make sense in a redraft league, no way am I give up two cheap, young assets plus Bernard for Hopkins (who I do think is a Top-5 wideout).

The upside is just too high on Matthews and Evans, plus the value given of three fantasy starters for one studly starter just doesn’t compute for me.

If I’m a contender at the deadline, I’m not looking to get back less starters than I’m giving up, unless I have a super deep bench. If making a deal like the above, though to get Hopkins means I have to start a player I can’t trust weekly in the playoffs to replace a guy I just traded while giving up multiple starters, the point differential Hopkins is giving me doesn’t matter. I’m not starting Nate Washington or Malcom Floyd in the playoffs without a serious down-the-stretch track record or injuries just to get myself a player like Hopkins.

6) Don’t be afraid of the one-year contract expiring player for several reasons.

A few weeks ago, a Twitter follower @naandrews19 sent me a few messages about how to value first year players. Nick was asking me how to value these in his league when others were so focused on multi-year players and suggested I write an article about it. First off, thanks Nick for the idea and for following me. Second, hopefully I can address the one-year expiring player, who I do believe has more value than your league counterparts think.

Nick was saying that most of his league was very afraid to trade their picks for “rental” players, guys on one-year deals. This is faulty logic to me. I know the tendency in leagues like this is to try to lock up a bunch of studs on multi-year deals. However, sometimes that blows up in an owners face. In fact, in your first few years, your best team strategy is probably to avoid getting yourself into bad contracts. Ask the owner of Charles Johnson about multi-year deals now and see what he says if he/she can get out a complete sentence without a bunch of expletives.

With that, let me be explicit. There are certain types of players worth trading your first-round draft picks for on expiring deals. Those players to me are guys that you’d consider putting the franchise tag on in 2016. If you already have an obvious franchise tag player based on your league dynamics, or the amount this newly acquired player would cost you in 2016, don’t fret. You still may be willing to part with a 2016 first rounder if you know that you will be in the bottom few picks of the first round and the player you’re getting is worth it. Logically, you’d prefer to give up a second rounder because the picks don’t snake, so you aren’t really giving up much from that standpoint with a second rounder. The happy go between may be to give up a second rounder and a player (either a mid-tier player or a devy guy if you have many of them).

In terms of examples, guys like Danny Woodhead (still currently in the Top 5 in PPR league scoring at running back) are prime examples of players who may not have a ton of future value but can make a significant contribution for your team towards a title.

7) Who is your biggest roadblock to winning a championship and what are they doing at the deadline to improve their team?

Sometimes you have to follow a game theory strategy and only make moves if you perceive your biggest roadblock is going to make them (or already has made them). As a contending team, you have a certain window to remain competitive, so keep that in mind in any deals made. That said, on my current team, I’d be more than willing to move a guy like Chris Conley and his6’3′, 205 lb frame and 4.35 40-time on a cheap multi-year deal if it netted me the piece I needed to put me ahead of my rival. If the right player was available and the other trading partner wanted someone else in the deal with Conley, I feel like a guy like Vernon Davis could be of interest in his new Denver locale.

If the other team is doing nothing, you may not need to do anything (sometimes doing nothing is actually the best strategy), but be acutely aware of where their weaknesses are and see how you really match up with them in a one-game playoff scenario

8) Non-contending teams should be looking to unload bad contracts as well as pick up future assets.

I feel like I’ve been banging this drum all year, but non-contending teams want three things in this order: 1) future draft picks 2) to rid themselves of bad contracts 3) developmental players. If you are a team that’s fallen on bad luck with injuries or non-performance but have a wealth at a certain position, perhaps you package that wealth with a bad contract (think guys like Michael Floyd or Victor Cruz) to get a combination of assets and contract relief. Heck, if you haven’t moved a player out for the season to IR, you can even trade them if they have future years (guys like Arian Foster) if you are thinking they won’t come back at the same level or at all. Like the NFL, however, you can’t trade players off of your IR on the RSO platform.

So, those are some of my thoughts as your league deadline approaches. I find myself currently to be a buyer in both leagues I’m in (I’m a jaw-dropping 8-0 in my writers league, dominating in total points scored and searching for an area to improve in a 10 team league and I’m 5-3 in my main league with the second highest point total). I don’t know if I’ll get any deals done in these leagues, but I certainly am thinking about potential offers at this point.

Feel free to reach out to me on Twitter @mattgoody2 to talk trade strategy, general questions, start/sit, whatever is on your mind RSO wise and good luck this week!